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this is going to sound silly but I need to know.

Kinda embarrassed to ask and I think I know the answer but going to ask anyway. At some point in the future hopefully sooner than later I am to be put on ovulation medication. Will that mean when they monitor me that when I am supposed to ovulate me and DH will have to bd-ing on that day? Meaning that specific day?

With Clomid and ovulation induction you have the following:
At the beginning of your period (normally day 2) you take Clomid for 5 days. On day 10 they do an internal scan as well to check if you are responding. Then either on that day or on day 12 you go back and you have a trigger injection, sometimes another scan. They then will ask you to have sex every day for the next 2/3 days. If you have too many follicles they tell you to abstain. It's always better to do it every 2/3 days anyway to have a constant sperm supply inside.
The monitoring changes depending on the clinics, some do more, some do less.